3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

Base Information

• Chemical Name: 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester
• CAS No.: 679005-38-0
• Molecular Formula: C₂₃H₂₈N₂O₆
• Molecular Weight: 428.485
• Mol file: 679005-38-0.mol

Synonyms:3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

Chemical Property of 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

There total 8 articles about 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 94.0%

3-[4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxy-5-nitrophenoxy]propionic acid benzyl ester (679005-37-9) → 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester (679005-38-0)

Guidance literature:

With tin(ll) chloride; In methanol; for 1h; Heating;

DOI:10.1016/j.bmcl.2003.12.017

Reference yield:

4-(2-benzyloxycarbonylethoxy)-5-methoxy-2-nitrobenzoic acid (679005-36-8) → 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester (679005-38-0)

Guidance literature:

Multi-step reaction with 3 steps

1: (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

2: 100 percent / Et₃N / CH₂Cl₂ / -30 - 20 °C

3: SnCl₂*2H₂O / methanol / 6 h / Heating

With oxalyl dichloride; triethylamine; N,N-dimethyl-formamide; tin(ll) chloride; In methanol; dichloromethane;

DOI:10.1021/jm051199z

Reference yield:

3-(4-carboxy-2-methoxy-5-nitrophenoxy)propanoic acid (219562-36-4) → 3-[5-amino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester (679005-38-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 56 percent / 4-toluenesulfonic acid / toluene / 3.5 h / Heating

2: (COCl)2; DMF / CH₂Cl₂ / 18 h / 20 °C

3: 100 percent / Et₃N / CH₂Cl₂ / -30 - 20 °C

4: SnCl₂*2H₂O / methanol / 6 h / Heating

With oxalyl dichloride; toluene-4-sulfonic acid; triethylamine; N,N-dimethyl-formamide; tin(ll) chloride; In methanol; dichloromethane; toluene;

DOI:10.1021/jm051199z

upstream raw materials:

3-[4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxy-5-nitrophenoxy]propionic acid benzyl ester

(S)-1-Pyrrolidin-2-yl-methanol

3-(4-carboxy-2-methoxy-5-nitrophenoxy)propanoic acid

benzyl alcohol

Downstream raw materials:

3-[5-tert-butoxycarbonylamino-4-((2S)-2-hydroxymethylpyrrolidine-1-carbonyl)-2-methoxyphenoxy]propionic acid benzyl ester

(11S,11aS)-8-(2-benzyloxycarbonylethoxy)-11-hydroxy-7-methoxy-5-oxo-2,3,11,11a-tetrahydro-1H,5H-pyrrolo[2,1-c][1,4]benzodiazepine-10-carboxylic acid tert-butyl ester